Acrylonitrile → 3-[(1-Benzylpyrrolidin-3-yl)amino]propanenitrile

HRID 1071609Notes

Reaction equation

HRID 1071609 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](#[N:17])[CH:15]=[CH2:16]>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:16][CH2:15][C:14]#[N:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 27566131-Benzyl-3-aminopyrrolidine

Product 1

HCID 223936893-[(1-Benzylpyrrolidin-3-yl)amino]propanenitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

4.00 g (22.7 mmol) of 1-benzyl-3-aminopyrrolidine was dissolved in 70 ml of methanol, 1.49 ml (22.7 mmol) of acrylonitrile was added thereto, and the mixture was heated to 70° C. After completion of the reaction, the reaction solution was evaporated, and the resulting crude product was subjected to 100 g of Cromatorex NH silica gel (ethyl acetate 100%), to give 4.60 g (20.1 mmol, 88.4%) of the title compound as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated

Sources & evidence

ORD record
ord-0ccad909758c4d6897ab318817c294cd
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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